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Is there a standard trade in value for the base Pro each year? Eg is it always $570 trade in value on launch day for the prior years model? Is does the trade in value change year over year?

It changes.
 
To me I tend to do the one-time payment of the Pro series iPhone each year and keep the old/previous phone in my collection. I did the iPhone upgrade program once and a few Apple Card monthly installments but I never liked the monthly payment even without interest.
 
Another vote for the iPhone Upgrade Program. Yes you could squeeze out a few more dollars elsewhere but Apple makes it seamless. You get the new phone and the box to send the old one back. I don't think about it at all and have no complaints.
 
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What if you unexpectedly die shortly after upgrading? All that you mentioned above is now irrelevant, but if you upgrade you get to spend an extra couple of days with your 16 pro max
That is a "what-if" that is as likely as the "what if you don't have any retirement savings or a tiny nest egg if you do survive to live up to an old retirement age?" So it isn't irrelevant at all.
 
Lol @ the virtue-signaling. Upgrade if your budget allows* and if you have the desire. Life is short. Find small joys wherever you can. If that's a new gadget, great!

*To be specific on the budget comment because I know I'm going to get whined at: Bills paid, emergency fund, retirement investments on track, etc.
 
I have been upgrading yearly since iPhone 7 and now have the iPhone 15 Pro Max. This year, I will not upgrade because the changes are minimal and phones look identical. I am going to slow the upgrades down to every 2 or 3 years. If you have a iPhone 11/12 then the upgrade might be justified. I should have stopped at the 13 Pro Max but wanted the new toy and now it's just not worth it.
 
Lol @ the virtue-signaling. Upgrade if your budget allows* and if you have the desire. Life is short. Find small joys wherever you can. If that's a new gadget, great!

*To be specific on the budget comment because I know I'm going to get whined at: Bills paid, emergency fund, retirement investments on track, etc.
I don't think you understand the definition of "virtue signaling." But ok, you do you.
 
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I tend to upgrade every two years. I am still on the iPhone 13 Pro but I'm not excited about this years model. I'd wait but I am also paying a higher rate now for the monthly Apple Care+ so that's a factor I need to math in.
 
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Upgrading every single year is really a waste of money (and effort)

These devices aren't changing that much year to year anymore
That's true. In the early 2000's phones had been getting smaller and smaller, so much so they needed to be flip phones. Then video came playable and the phones got bigger to accommodate larger screen size, but were now slimmer and with reduced bezel. Nowadays they seem to have reached their desired abilities with them all being quite similar with them being small enough to carry in your pocket yet with screens big enough for watching videos. I doubt that phone sizes will change much other than foldable phones.
 
While this is NOT how I handle updates (I am more “keep it till is dies” type). But for those who do practice frequent regular updates with trade-ins, I think a better way to visualize the concept is as a lease vs buy situation. Good for some people, especially useful for businesses.
 
While this is NOT how I handle updates (I am more “keep it till is dies” type). But for those who do practice frequent regular updates with trade-ins, I think a better way to visualize the concept is as a lease vs buy situation. Good for some people, especially useful for businesses.
I generally agree, but something I like about the program is that if you decide to keep paying for 2 years instead of trading it in then you own the phone outright after that.
 
I upgrade every year since iPhone X and always recoup 55% of the original cost. I sell my iPhone pristine without a single scratch and battery health at 95-100%.
 
I’m trying to get more scheduled/organized about regular yearly iPhone upgrades and am eager to hear some best practices from the forum on how to optimize it and how to minimize the expense.

Every third year I have been taking advantage of AT&T’s $1000 off after eligible trade in and that works well for me but am now trying to assess my approach in the other two years. Does buying outright and selling on eBay or Swappa make the most sense, or go with the iPhone Upgrade Program, or some other approach?
I have used AT&T Next for as long as it has been around, which is their equivalent to the iPhone Upgrade Program. I pay a modest monthly fee to own my iPhone on top of my service bill, and come iPhone season I order the new one, send in the old one, and keep going. Over the course of a year (with no interest) I pay less than half of what the phone actually costs to use it for a year. Similar experience, yet far more convenient and financially sensible than buying it outright and selling it a year later. Should I ever get tired of upgrading, I can simply continue to pay for the phone monthly until it's paid off. It's a very affordable and convenient way of upgrading every year. No complaints.
 
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I have used AT&T Next for as long as it has been around, which is their equivalent to the iPhone Upgrade Program. I pay a modest monthly fee to own my iPhone on top of my service bill, and come iPhone season I order the new one, send in the old one, and keep going. Over the course of a year (with no interest) I pay less than half of what the phone actually costs to use it for a year. Similar experience, yet far more convenient and financially sensible than buying it outright and selling it a year later. Should I ever get tired of upgrading, I can simply continue to pay for the phone monthly until it's paid off. It's a very affordable and convenient way of upgrading every year. No complaints.
This is exactly what I do on T-Mobile! I expect that many, many people do this, so I don’t understand the frequency of “how can you afford to do this”… the phone costs me $50 a month until I meet the requirements to upgrade after 12 months/payments, which is half the cost of the phone, then I upgrade and send in the old one and the new phone payment replaces my old one at the same rate—I always get the base Pro Max which is always (hopefully) $1200 every year.

Paying $50 a month of use the phone is much more palatable to me than paying $1200 outright for a phone I’ll want to replace in a year—I could then sell it, but that involves dealing with people which is very no bueno 😂
 
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This is exactly what I do on T-Mobile! I expect that many, many people do this, so I don’t understand the frequency of “how can you afford to do this”… the phone costs me $50 a month until I meet the requirements to upgrade after 12 months/payments, which is half the cost of the phone, then I upgrade and send in the old one and the new phone payment replaces my old one at the same rate—I always get the base Pro Max which is always (hopefully) $1200 every year.

Paying $50 a month of use the phone is much more palatable to me than paying $1200 outright for a phone I’ll want to replace in a year—I could then sell it, but that involves dealing with people which is very no bueno 😂
Yes. And annual is not the only option either, if someone wants to pay a little less per month they can choose an 2 year upgrade cycle. Though I believe 12 months is the best value all around.
 
Yes. And annual is not the only option either, if someone wants to pay a little less per month they can choose an 2 year upgrade cycle. Though I believe 12 months is the best value all around.
Yep :) I choose the 12 month because getting a shiny new toy every year makes the brain chemicals do the good thing, even if the updates are iterative. This year I am very excited for the capture button because I do a lot of skateboard filming and currently, when I need to zoom in and out, I often accidentally tap the wrong zoom button and it messes up my video. I can’t watch the skater move AND look at the zoom options simultaneously. I look forward to seamless zooming!
 
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I have used AT&T Next for as long as it has been around, which is their equivalent to the iPhone Upgrade Program. I pay a modest monthly fee to own my iPhone on top of my service bill, and come iPhone season I order the new one, send in the old one, and keep going. Over the course of a year (with no interest) I pay less than half of what the phone actually costs to use it for a year. Similar experience, yet far more convenient and financially sensible than buying it outright and selling it a year later. Should I ever get tired of upgrading, I can simply continue to pay for the phone monthly until it's paid off. It's a very affordable and convenient way of upgrading every year. No complaints.
Can you take advantage of the credits from the $1000 off deal every third year AND be on AT&T next?
 
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